I was always awe-stricken by the likes of Glenn Hoddle and others from the Boys of White Hart Lane era but 1987 was the year that truly pulled me in and I've never let go. It was also the year that broke Tottenham Hotspur.

We lost at Wembley (in the FA Cup) for the first time ever. The less said about the League Cup semi the better. What followed was a couple of decades of mismanagement and transition. We went from being a pioneering club off the field and cup kings on it to the verge of bankruptcy and perpetually mediocre mid-table misadventures. We still punctured the footballing calender with a cup final or two and many brilliant players in amongst the woeful.

When I was a young lad I idolised Paul Gascoigne. He was the first player I truly gravitated towards in terms of obsession. When Gazza joined in 1988 I found myself mesmerised. That was the last time I was truly in love with football. Disappointment and dejection was to become synonymous with the club whilst others in far healthier positions structurally went on to grasp the opportunities of the birth of the Sky Sports era.

We've continued to puncture that calender. It's been a hard old slog with plenty of lows and the occasional stunning high. The best years of my life ran parallel to the desolate footballing 1990s but the only ecstasy that remained consistent was in the nightclubs rather than at the Lane. Aside, of course, from the memorable early years of that decade and its closure (giving us two cups).

When I think back I see Gazza, Waddle, Lineker, Kilnsmann, Ginola and other icons of the club. Players that gave us joy lived up to the great players of past generations. However, much like the pills I was taking to the tunes of Sasha and Digweed, the footballing ecstasy wasn't cut pure. The individualistic class of the select few felt like it was mixed with ketmaine, leaving us numb to the constant pain. We had to deal with the High Court drama of Sugar v Venables, persistent managerial debacles, the odd flirtation against relegation and plenty of FA Cup semi-final heartbreak. Everything was broken. Even the icons. Even Gascoigne, my hero.

Shift forward another generation and only Spurs could produce one of the best centre-backs this country has never had. Ledley King was a majestic giant of a man, gentle in manner yet so commanding in presence. He elevated average players to outstanding ones when they stood beside him. The ease in which he made the difficult appear effortless was a once in a life-time quality. Yet how many appearances and caps have been stolen thanks to that dodgy knee? It's phenomenal that he hardly trained in his latter years before swapping his Lilywhite shirt for an ambassadorial role.

In modern times it's hard to idolise anyone. I'm a grown man so I've moved on from collecting newspaper articles and copies of Shoot and Match. Loyalty is a rude word and the internet has connected us all. There is no mystery and no genuine anticipation thanks to the 24/7 coverage and commentary of every nuance of football. We microscopically analyse and critique all details. Players become commodities. Financial ones for the club and mostly scapegoats for the supporters. Even modern day heroes leave us despondent. Dimi Berbatov, Luka Modric, Gareth Bale...great Spurs players yet bitterness tarnishes their legacy as they look back to the stepping stone the club was for them. They didn't quite complete their journey with us and hitched a ride with another instead. We weren't exactly sure of our destination so you can hardly blame them. It still left us feeling empty each time. It always does regardless of when we can see it coming.

We're left with the lesser mortals to place our hope with for the remainder of our circular journey. Unsung players, the occasional kid or experienced pro that punches above their weight. Younes Kaboul doesn't quite fit into the upper echelons of our history. He wasn't consistent or great enough to be idolised or to be spoken in the same way as Ledley and others. We even sold him and then signed him back. Like so many before him, he was also broken.

When he joined us for the first time he had the physical attributes but lacked discipline. When he left that old friend disappointment hugged me mockingly. I still believed he possessed untapped potential. He then found form and identity away from WHL and when he returned he did so as a man rather than that naive erratic boy we knew. What followed was yet another monumental tease of talent that never fulfilled itself.

He was beastly in the 2012 season and when alongside King, there was a measure of immensity that we so rarely get treated to. He was equally a leader, yet perhaps prone to mental fragility that Ledley hardly ever suffered from. But the partnership itself was a rarity. Kaboul's injury issues gave us a prince to sit alongside a king whilst watching a leaderless army that lacked generals take to the field of battle.

There were highs in amongst the lows. Our story arc since 1987 has never failed to deliver those punctured moments we love to cherish. Football is and always will be about the moments. Be it that occasional cup final or a slice of glory in the form of an iconic goal or a famous derby win or just aiming high enough that even in failure...well, you know about the echoes. I don't need to preach to the converted.

Younes gave us that winning goal at the Emirates in an absolute classic. He crossed for Peter Crouch to head in at City away that gave us the much sought-after promised land we had been searching for. Both wonderful moments even if that probably warrants another mocking hug from our old friend 'disappointment' that persistently waves the silverware of other clubs in our faces.

Yes, his recent captaincy was a low point. The rumours concerning behind the scenes dressing room disruptions, equally sad. I prefer to remember him running to the dugout looking to celebrate with Ginola with Martin Jol getting in the way after equalising to make it 4-4 in the 125th anniversary match. A young man of 21, the world at his feet, unsullied. Goodbye brother, thanks for the memories. You are broken, but you were Tottenham.